Apomorphine hydrochloride

Base Information

• Chemical Name: Apomorphine hydrochloride
• CAS No.: 314-19-2
• Deprecated CAS: 5896-07-1
• Molecular Formula: C17H17 N O2 . Cl H
• Molecular Weight: 303.788
• European Community (EC) Number: 206-243-0,627-402-4
• NSC Number: 11442
• UNII: 9K13MD7A0D
• DSSTox Substance ID: DTXSID5040598
• Wikidata: Q27272658
• NCI Thesaurus Code: C80572
• RXCUI: 71225
• ChEMBL ID: CHEMBL1616
• Mol file: 314-19-2.mol

Synonyms:Apokinon;Apomorphin Teclapharm;Apomorphin-Teclapharm;Apomorphine;Apomorphine Chloride;Apomorphine Hydrochloride;Apomorphine Hydrochloride Anhydrous;Apomorphine Hydrochloride, Anhydrous;Apomorphine Hydrochloride, Hemihydrate;Britaject

Chemical Property of Apomorphine hydrochloride

Chemical Property:

• Vapor Pressure: 1.87E-10mmHg at 25°C
• Melting Point: >250℃
• Boiling Point: 473.4°Cat760mmHg
• Flash Point: 268.8°C
• PSA: 43.70000
• Density: g/cm³
• LogP: 3.58980
• Storage Temp.: Store at RT
• Solubility.: ≥1.08 mg/mL in EtOH with ultrasonic; ≥12.9 mg/mL in DMSO; ≥5.12 mg/mL in H2O
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 303.1026065
• Heavy Atom Count: 21
• Complexity: 374

Purity/Quality:

99%, ^*data from raw suppliers

(R)-(-)-ApomorphineHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1CCC2=C3C1CC4=C(C3=CC=C2)C(=C(C=C4)O)O.Cl
• Isomeric SMILES: CN1CCC2=C3[C@H]1CC4=C(C3=CC=C2)C(=C(C=C4)O)O.Cl
• Recent ClinicalTrials: Apomorphine in Severe Brain-injured Patients
• Recent EU Clinical Trials: Etude pharmacocinétique de l’apomorphine en perfusion sous-cutanée continue diurne chez le patient parkinsonien équilibré sous traitement
• Uses: Emetic. (R)-(-)-Apomorphine Hydrochloride is a prototypical dopamine agonist. Potential treatment for Parkinson’s disease.
• Therapeutic Function: Emetic, Expectorant, Hypnotic, Antiparkinsonian, Dopamine agonist
• Clinical Use: Treatment of refractory motor fluctuations in Parkinson’s disease
• Drug interactions: Potentially hazardous interactions with other drugs Antihypertensives: enhanced hypotensive effect. Domperidone: possible increased risk of ventricular arrhythmias. 5HT3 -receptor antagonists: possibly increased hypotensive effects with ondansetron. Nitrates: enhanced hypotensive effect.

Technology Process of Apomorphine hydrochloride

There total 21 articles about Apomorphine hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

MORPHIN (57-27-2) → apomorphine hydrochloride (314-19-2,41035-30-7,5896-07-1)

Guidance literature:

With hydrogenchloride; calcium chloride; In water; at 45 - 145 ℃; for 2h; Inert atmosphere;

Reference yield:

neomorphine (86709-01-5) → apomorphine hydrochloride (314-19-2,41035-30-7,5896-07-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent

2: 85 percent / pyridine / 1.) 0 deg C, 2 h, 2.) r.t., 24 h

3: 80 percent / tetrabutylammonium fluoride / acetonitrile / 3 h / Heating

4: 1.) methanesulfonic acid, 2.) hydrochloric acid / 1.) 100 deg C, 30 min, 2.) ethanol

With pyridine; hydrogenchloride; methanesulfonic acid; tetrabutyl ammonium fluoride; In acetonitrile;

Reference yield:

3-O-acetylneomorphine (86680-37-7) → apomorphine hydrochloride (314-19-2,41035-30-7,5896-07-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / pyridine / 1.) 0 deg C, 2 h, 2.) r.t., 24 h

2: 80 percent / tetrabutylammonium fluoride / acetonitrile / 3 h / Heating

3: 1.) methanesulfonic acid, 2.) hydrochloric acid / 1.) 100 deg C, 30 min, 2.) ethanol

With pyridine; hydrogenchloride; methanesulfonic acid; tetrabutyl ammonium fluoride; In acetonitrile;

upstream raw materials:

(3,4-dimethoxyphenoxy)trimethylsilane

methyl-N-(benzyl-methyl)-formamide

10,11-dimethoxy-6-methyl-aporphane

phenethylamine

Downstream raw materials:

Di-isobutyryl-apomorphin

5,6,6a,7-tetrahydro-6-methyl-4H-dibenzo[de,g]quinoline-10,11-diol

(R)-MDO-Apomorphine

8-[2-(methylamino)-ethyl]-phenanthrene-3,4-dioxide

Refernces

• 1、 Muraca, Ana Carolina A.,Perecim, Givago P.,Rodrigues, Alessandro,Raminelli, Cristiano. "Convergent Total Synthesis of (±)-Apomorphine via Benzyne Chemistry: Insights into the Mechanisms Involved in the Key Step". . p. 3546 - 3557. Retrieved 2017/08/15.
• 2、 Berenyl,Hosztafi,Makleit,Molnar. "Preparation of demethoxyoripavine and its conversion into N-substituted N-demethylapomorphine derivatives". . p. 51 - 60. Retrieved 2007/10/02.